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High throughput solid-phase screening of bacteria with cyclic amino alcohol deamination activity for enantioselective synthesis of chiral cyclic β-amino alcohols

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Abstract

Objectives

To screening of bacteria with cyclic amino alcohol deamination activity for enantioselective synthesis of chiral cyclic β-amino alcohols.

Results

A new strain named Arthrobacter sp. TYUT010-15 with the (R)-selective deamination activity of cyclic β-amino alcohol has been isolated from nature via a high throughput solid-phase screening method. The reaction conditions of TYUT010-15 were optimized. Using the resting cell of TYUT010-15 as the catalyst, kinetic resolution of trans-2-aminocyclopentanol, trans-2-aminocyclohexanol and cis-1-amino-2-indanol was carried out to afford (1S, 2S)-trans-2-aminocyclopentanol, (1S, 2S)-trans-2-aminocyclohexanol and (1R, 2S)-cis-1-amino-2-indanol in > 99% ee and 49.6–50% conversion. Four aromatic β-amino alcohols and two amines were also resolved, (S)-β-amino alcohols and (R)-amines were obtained in > 99% ee. Preparation experiment was conducted with 200 mM (23.2 g L−1) racemic trans-2-aminocyclohexanol, yielding the desired (1S, 2S)-trans-2-aminocyclohexanol in 40% isolated yield, > 99% ee and 5.8 g L−1 d−1 space time yields.

Conclusions

This study provides a high throughput solid-phase method for screening of bacteria with cyclic amino alcohol deamination activity and a first example for practical preparation of chiral cyclic β-amino alcohol by Arthrobacter sp. TYUT010-15.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (Grant No. 21772141) and the Shanxi Province Science Foundation for Youths (Grant No. 201701D221042).

Supporting information

Supplementary Table 1—Kinetic resolution of racemic trans-2-aminocyclohexanol 1b by the isolated strains.

Supplementary Figure 1—Phylogenetic dendrogram for isolated strain based on the 16S rRNA gene sequence.

Supplementary Figure 2 to 9—Chiral GC analysis of 1a–3b.

Supplementary Figure 10—Chiral HPLC analysis of cis-1c.

Author information

Authors and Affiliations

  1. Department of Biological and Pharmaceutical Engineering, College of Biomedical Engineering, Taiyuan University of Technology, No.79 West Yingze Street, Taiyuan, 030024, Shanxi, People’s Republic of China

    Ya-Wen Chang, Jian-Dong Zhang, Xiao-Xiao Yang, Jing Li, Shuang-Ping Huang, Cao-Feng Zhang & Hong-Hong Chang

  2. College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan, 030024, Shanxi, People’s Republic of China

    Ya-Wen Chang & Xing-Mei Guo

  3. Department of Environmental Engineering, Taiyuan University of Technology, Taiyuan, 030024, Shanxi, People’s Republic of China

    Li-Li Gao

  4. Laboratory of Biocatalysis and Bioprocessing, State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, People’s Republic of China

    Jian-He Xu

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  1. Ya-Wen Chang
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Correspondence to Jian-Dong Zhang.

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Chang, YW., Zhang, JD., Yang, XX. et al. High throughput solid-phase screening of bacteria with cyclic amino alcohol deamination activity for enantioselective synthesis of chiral cyclic β-amino alcohols. Biotechnol Lett 42, 1501–1511 (2020). https://doi.org/10.1007/s10529-020-02869-2

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